Once temperatures drop, many of us start daydreaming about chasing the sun on balmy holidays to the Canary Islands, Cyprus and even further afield to South America and Dubai.
But what if instead of fleeing the onset of cold weather, we embrace it, seeking out trips where a true white Christmas is all but guaranteed?
As someone who lives on the rainy west coast, Regan said that "anywhere I can go that it's not raining, that is the winter experience I want to have, so as long as it's dry, I think we all have a better time".
She added that other countries "don't seem to get as surprised as we do" once winter hits, and know how to navigating the changing seasons possibly a bit better.
"It's like they're prepared for it, it's cold but it's not damp and I think that's the big difference as Irish people, when we go there", she said.
Of course, not everyone has the extra money for a winter break, especially with Christmas around the corner, so Regan shared her tips for cutting costs. Chief among them is skipping the hotel for a hostel. If the word brings back memories of bleak university holidays, fear not: Regan actually means hostel-hotel-hybrids.
"I'm not talking about you going into a dorm there with 45 other people", she laughed. "Just when you're going in a city break you're probably going for two days, maybe three, max. So your accommodation is not important because you want to drop your bag, get our and experience where you're going.
"I would put more money into my eating experiences or doing a tour than I would just staying in a high-end accommodation."
As for activities, Regan recommends a walking tour, despite the weather. "The Europeans just get it, they're like, wear a rain jacket for the weather." She also notes how walking tours are still popular in Ireland in the winter too, and are a great way of getting your bearings in a new city.
Here are her top three cities to visit in winter:
Copenhagen, Denmark
"It's so chic", Regan said about this eternally stylish city. "Everyone is just wearing navy and cashmere and long jackets and boots and they all just look stunning. Don't wear colour when you go to Copenhagen or they'll know you're not from there."
Noting how it's an outdoorsy city in any weather, with bikes aplenty, Regan said, "they know how to embrace the winter".
She spotlighted the Tivoli Gardens, a multipurpose space in the city centre that shifts with the seasons, becoming a Christmassy hub in winter, filled with food stalls, rides and more.
As for cost of living, Regan said "it's the same as Ireland now", and filled with exceptional food, coffee and pastries.
Amsterdam, The Netherlands
Although widely known as a party destination, Regan suggested staying on the west side of the city which is more "neighbourhood-focused".
"Great bike culture, the canals, and a really really nice easy pace of life, as well. Very friendly, they're very family-centric too, and because it's so accessible, it's so easy to get around." Don't miss the neighbourhood markets each Saturday, Regan said, which is great for vintage thrifting.
The Anne Frank Museum is as incredible as it's said to be, Regan noted. "It's really intense but in a good way, you get the whole history of what happened and you go into the house."
On top of this, the city has a winter-specific festival, the Amsterdam Light Festival, which is now in its 12th year. Spanning across the city from mid-November to January it's a mix of ticketed events and free ones, and this year the festival focuses on AI and tech.
Paris, France
As one of the busiest cities in Europe, the City of Light is flooded with tourists each year but Regan suggests going in the winter for slightly smaller crowds.
"If you want to get into the major tourist attractions there, the lines are literally halved in the winter time", she said, adding that winter weather in Paris is especially pleasant and perfect for indulging in its famous café culture.
When hunting down a good meal in Paris, however, Regan cautions against relying too much on social media and what's trending at the moment. "People are now queuing outside to get their shot with the food outside these cafés, they're just ruining it."
For more tips on winter travel, listen back to the full interview above.